benzyl (3S)-3-[benzyl[(1S)-1-phenylethyl]amino]butanoate -Drug Synthesis Database

【结构式】

【分子编号】46909

【品名】benzyl (3S)-3-[benzyl[(1S)-1-phenylethyl]amino]butanoate

【CA登记号】

【分子式】C₂₆H₂₉NO₂

【分子量】387.5218

【元素组成】C 80.59% H 7.54% N 3.61% O 8.26%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The desired enantiomer was prepared by two chiral routes. Monoalkylation of (S)-alpha-methylbenzylamine (I) with benzyl bromide in N,N'-dimethylpropyleneurea gave the chiral secondary amine (II). Diastereoselective Michael addition of the lithium amide of (II) to benzyl crotonate (III) provided adduct (IV). The chiral ester (IV) was then reacted with the Grignard reagent (V) to yield the diaryl carbinol (VI). This was subsequently dehydrated to (VII) using H2SO4 in glacial HOAc. Double bond reduction and N-debenzylation of (VII) over Pearlman抯 catalyst provided the target primary amine, which was finally isolated as the hydrochloride salt.

参考文献中间体

合成目标

【1】 Moe, S.T.; DelMar, E.G.; Smith, D.L.; et al.; Chiral synthesis and pharmacological evaluation of NPS 1407: A potent, stereoselective NMDA receptor antagonist. Bioorg Med Chem Lett 2000, 10, 21, 2411.
【2】 Moe, S.T.; Mueller, A.L. (NPS Pharmaceuticals, Inc.); Cpds. active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases. WO 9856752 .
【3】 Moe, S.T.; Mueller, A.L.; Vanwagenen, B.C.; Barmore, R.M.; Delmar, E.G.; Artman, L.D.; Balandrin, M.F.; Smith, D.L. (NPS Pharmaceuticals, Inc.); Cpds. active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases. WO 9746511 .
【4】 Barmore, R.M.; DelMar, E.G.; Balandrin, M.F.; VanWagenen, B.C.; Artman, L.D.; Mueller, A.L.; Moe, S.T. (NPS Pharmaceuticals, Inc.); Cpds. active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases. US 6071970 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	20042	(1S)-1-phenyl-1-ethanamine; (1S)-1-phenylethylamine		C₈H₁₁N	详情	详情
(II)	38470	(1S)-N-benzyl-1-phenyl-1-ethanamine; N-benzyl-N-[(1S)-1-phenylethyl]amine	38235-77-7	C₁₅H₁₇N	详情	详情
(III)	46908	benzyl (E)-2-butenoate		C₁₁H₁₂O₂	详情	详情
(IV)	46909	benzyl (3S)-3-[benzyl[(1S)-1-phenylethyl]amino]butanoate		C₂₆H₂₉NO₂	详情	详情
(V)	35384	bromo(3-fluorophenyl)magnesium		C₆H₄BrFMg	详情	详情
(VI)	46910	(3S)-3-[benzyl[(1S)-1-phenylethyl]amino]-1,1-bis(3-fluorophenyl)-1-butanol		C₃₁H₃₁F₂NO	详情	详情
(VII)	46911	(2S)-N-benzyl-4,4-bis(3-fluorophenyl)-N-[(1S)-1-phenylethyl]-3-buten-2-amine; N-benzyl-N-[(1S)-3,3-bis(3-fluorophenyl)-1-methyl-2-propenyl]-N-[(1S)-1-phenylethyl]amine		C₃₁H₂₉F₂N	详情	详情

Extended Information